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TECHNICAL DATA SHEET Date of Issue: 2017/01/09

Zinc Chloro 2,2,6,6- { error: file not found: D:\WWI\graphics\408613.jp Tetramethylpiperidide g } Complex, typ. 17 % solution in THF (typ. 0.7 M)

Molecular Formula C₉H₁₈ClZnN • LiCl

Product Number 408613

APPLICATION Selective deprotonation of arenes and heteroarenes.

Arenes and heteroarenes are typically deprotonated by a directed lithiation using organolithium compounds or organolithiumamides (e.g. LDA). The high reactivity and nucleophilicity of these reagents often result in unwanted side reactions and preludes the presence of sensitive functional groups like or ketones. Additionally, such deprotonation reactions often require low temperatures leading to higher production costs on larger scale.

Due to their low kinetic basicity zinc-amides tolerate a lot of functional groups.

FURTHER INGREDIENTS

Tetrahydrofuran CAS-No. 109-99-9 EC-No. 203-726-8 Zinc chloro 2,2,6,6-tetramethylpiperidide lithium chloride complex (1:1) CAS-No. 1145881-09-9 EC-No. not registered Lithium chloride CAS-No. 7447-41-8 EC-No. 231-212-3

SPECIFICATION active base as TMP-ZnCl 16.0 - 18.5 % w/o LiCl

Zn 0.80 - 0.95 mmol/g

The information presented herein is believed to be accurate and reliable, but is presented without guarantee or responsibility on the part of Albemarle Corporation and its subsidiaries and affiliates. It is the responsibility of the user to comply with all applicable laws and regulations and to provide for a safe workplace. The user should consider any health or safety hazards or information contained herein only as a guide, and should take those precautions which are necessary or prudent to instruct employees and to develop work practice procedures in order to promote a safe work environment. Further, nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the herein materials or processes in violation of existing or future patent.

Technical data sheets may change frequently. You can download the latest version from our website www.albemarle-lithium.com. Please contact us at www.albemarle-lithium.com/contact with questions.

Zinc Chloro 2,2,6,6-Tetramethylpiperidide Lithium Chloride Complex, typ. Page 2 / 3 17 % solution in THF (typ. 0.7 M) Product Number: 408613 Date of Issue: 2017/01/09

molar ratio Zn/Li 0.9 – 1.1

METHOD OF ANALYSIS

Active base: Titration with benzoic (modified Watson-Eastham titration). Detailed description is available on request.

PHYSICAL PROPERTIES

Appearance liquid Color brownish clear to cloudy Flash point -21.2 °C (Tetrahydrofuran)

Boiling point/boiling 66 °C (Tetrahydrofuran) range 0.95 g/cm3 at 20 °C Water solubility (Not applicable) Molecular weight 283.51 g/mol

Thermal Stability decomposition above 20°C

Additional Physical Molecular weight: Properties TMP-ZnCl 241.11 g/mol LiCl 42.4 g/mol

HANDLING & STORAGE

Handling Organozinc compounds should only be handled under inert gas ( or ). Never add water, or oxidizing materials to the product. In case of fire use dry extinguishers on basis of chloride or powder. Never use water or CO2-extinguishers. Pay attention to official Safety regulations (see also: 'Transport regulations' and 'Marking').

Storage Store in well ventilated areas in tightly closed containers. As material decomposes slowly above room temperature recommended storage temperature is below 20 °C.

The information presented herein is believed to be accurate and reliable, but is presented without guarantee or responsibility on the part of Albemarle Corporation and its subsidiaries and affiliates. It is the responsibility of the user to comply with all applicable laws and regulations and to provide for a safe workplace. The user should consider any health or safety hazards or information contained herein only as a guide, and should take those precautions which are necessary or prudent to instruct employees and to develop work practice procedures in order to promote a safe work environment. Further, nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the herein materials or processes in violation of existing or future patent.

Technical data sheets may change frequently. You can download the latest version from our website www.albemarle-lithium.com. Please contact us at www.albemarle-lithium.com/contact with questions.

Zinc Chloro 2,2,6,6-Tetramethylpiperidide Lithium Chloride Complex, typ. Page 3 / 3 17 % solution in THF (typ. 0.7 M) Product Number: 408613 Date of Issue: 2017/01/09

TRANSPORT & PACKAGING

UN number 2924

ADR Class: 3 PG: II Label: 3 (8)

RID Class: 3 PG: II Label: 3 (8)

IMDG Class: 3 PG: II Label: 3 (8)

IATA_C Class: 3 PG: II Packing instruction (cargo aircraft): 363

IATA_P Class: 3 PG: II Packing instruction (passenger aircraft): 352

Hazard pictograms

Signal Word Danger H&P Phrases See Safety Data Sheet

Labelling The labelling is according to EU-GHS classification ((EG) 1272/2008) and may vary in other countries. Please refer to the respective Safety Data Sheet for your country.

Packaging

Glass bottles of 100, 250, 500, and 1,000 ml. bottles and containers with volumes of 7.4 l, 27 l, 127 l or 450 l. For safety reasons these are filled to a maximum of 90 %. drums with 200 l net volume.

OTHER INFORMATION

Further Related Safety Data Sheet Documents Our brochure(s) Lithium & Amides

Remarks References / Literature:

T. Bresser, G. Monzon, M. Mosrin, P. Knochel, Org. Process Res. Dev. 2010, 14, 1299 M. Mosrin, T. Bresser, P. Knochel, Org. Lett. 2009, 11, 3406 T. Bresser, M. Mosrin, G. Monzon, P. Knochel, J. Org. Chem. 2010, 75, 4686 F. Gosselin, S. J. Savage, N. Blaquiere, S. T. Staben, Org. Lett. 2012, 14, 862

The information presented herein is believed to be accurate and reliable, but is presented without guarantee or responsibility on the part of Albemarle Corporation and its subsidiaries and affiliates. It is the responsibility of the user to comply with all applicable laws and regulations and to provide for a safe workplace. The user should consider any health or safety hazards or information contained herein only as a guide, and should take those precautions which are necessary or prudent to instruct employees and to develop work practice procedures in order to promote a safe work environment. Further, nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the herein materials or processes in violation of existing or future patent.

Technical data sheets may change frequently. You can download the latest version from our website www.albemarle-lithium.com. Please contact us at www.albemarle-lithium.com/contact with questions.